


Challenges

by ChocolateKid



Category: Supernatural
Genre: Butt Plugs, Challenges, Cruel Castiel, Friends With Benefits, Kinda, Light Dom/sub, M/M, Object Penetration, Orgasm Delay/Denial, PWP, Plot What Plot/Porn Without Plot, Public Orgasm, Sex Toys, Shameless Smut, Smut, rollercoaster
Language: English
Status: Completed
Published: 2017-01-03
Updated: 2017-01-03
Packaged: 2018-09-14 12:47:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,276
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9182437
Author URL: https://archiveofourown.org/users/ChocolateKid/pseuds/ChocolateKid
Summary: Castiel has another challenge for Dean: Wear a butt plug for the majority of the day without coming.





	

**Author's Note:**

> Here's another smutty one shot. I hope you like it!

**Dean's POV**

It was time again. Time for one of the little games Cas and I had started playing a while ago. While not being in a relationship, we regularly felt the need to get some stuff out of our system and the pleasure we got from our games was always a great way to relieve the stress we both felt.

Last night, it had been Cas's turn to think of a challenge. And I swear, said challenge was gonna be the death of me.

I was sitting in the Impala with Cas riding shotgun, the butt plug he had wanted me to wear worked deep inside of me. It was a big one, approximately the size of Cas's dick, if not a little bigger, and I was slowly dying on the inside. My dick had been in a state of full hardness since the moment I opened myself up and thanks to its special form, it had been pressing right into my prostate for the last hour.

The thing was that I knew I was not gonna get release anytime soon and it made me go almost crazy. Cas had wanted me to wear it the majority of the day, until he decided it was time for me to get satisfaction. And I knew he'd be cruel about it.

Driving down the lane, I suddenly hit a bump in the road that made the car jerk slightly and I moaned loudly as the plug hit my prostate hard. It was horrible, with every move I made I felt the plug work itself in deeper, pressing against my prostate harder. Hitting a bump was almost too much and I knew there were desperate tears in my eyes by now.

"Could you stop at the side of the road, please?" Cas said suddenly. "I'm afraid I need to urinate."

I only nodded in silent agony and left the main road to stop at the side of a forest. Nobody was in sight but I didn't even notice it, I was too focused on the feeling of that thing in me.

Cas left the car and I groaned inwardly. It was bad enough to resist jerking off while driving when Cas was right next to me; without him and with nothing to do, it was gonna be even harder.

Involuntarily, I shifted in my seat. Big mistake. I gasped when I felt the plug shift inside of me, caressing my magic spot in just the right places and I couldn't help but do it again and moan in pleasure. My hand found its way to my crotch, gripping at my rock hard dick through my jeans, longing for friction. Cas was gonna punish me for this later but I really didn't care at the moment.

Just as I had that thought, I heard the car door open again and I knew Cas was back. And he had seen. I looked into his eyes and saw the disapproving look in them as he stared at where my hand was currently lying. He glanced up and firmly shook his head.

"Cas-" I started but he stayed persistent.

"You've been bad, Dean. I told you not to do it and you were about to anyway. You need to be punished," he said matter-of-factly. I forced my hand away from my crotch and moaned. Cas's punishments were almost better than the challenges itself, even though he didn't always allow me to come. I just hoped this time would be one of the rare times he did let me.

"Yes, Cas, please, I know, I need to be punished, I've been so bad," I mumbled frantically and waited for him to give me instructions.

"Take out your dick," he ordered and I quickly did as told. The touch didn't help my situation and it especially didn't help when Cas added, "Now move your hips."

I shifted in the seat, feeling the plug push in and out with every move I made and I moaned and panted along to the sensations. I wasn't gonna last long and the anticipation had been killing me for an hour already, so I started picking up speed when Cas interrupted me.

"Don't come just yet," he said and I suppressed a sob at his words. "Keep moving though."

I slowed down my movements, hoping to last at least a little longer than two seconds, and it made my skin crawl with exhaustion. _Don't come_ , I told myself over and over again. _Don't_.

I slowed down my movements to a minimum and concentrated on thoughts about dirty socks in my laundry but then socks made me think about how they're kinda shaped like dicks and how good it would feel to have one over mine right now, and I groaned in anger. This wasn't helping. I wouldn't last. I was gonna--

"Stop," Cas finally said and I ripped my hand away from my dick, panting heavily. I sat as still as I could to avoid any and all sensations on my prostate until my dick calmed down enough for me to think rationally again. Cas apparently kept his promise about me having to last the majority of the day. Damn it.

After a few minutes, in which I finally managed to calm down my erratic breathing, Cas spoke up again.

"Now put your pants back on and get on the road again. We have plans after all."

I did as I was told, moving slowly, as I was still in a state of uncomfortable hardness. I turned the key in the ignition and winced when I felt the dreaded vibration of the engine but I managed to control myself.

Then I steered the vehicle back on the street and towards our destination.

* * *

 "So," I said after I finally found a parking spot and turned to look at Cas.

"So," he responded, grinned at me and opened the car door. "Let's go!"

I groaned and followed him reluctantly. I had a very bad feeling about this place.

I hurried after Cas while trying to keep the plug from shifting and simultaneously trying to avoid looking as if I shit myself. Standing in front of the gates, I saw the dreaded sign looming over me...

 _Disney World_.

"I'll get the tickets," Cas said and I nodded numbly as he left. I was so going to die.

* * *

 Half a day later, I was finished riding all the more harmless rides because Cas had let me decide what to do, generous as he was. The next one though, he had wanted to choose.

And that's how we ended up in line of some big ass rollercoaster and I was already scared shitless. Not only because I had a freaking plug in my butt that made me feel every movement but also because I was _kinda_ afraid of heights, too...

"It's alright, Dean, you'll be okay," Cas assured me and gently caressed my back.  "And right after this rollercoaster, we'll drive home and get rid off that thing in your ass," he promised, only slightly lowering his voice at the end of the sentence. I whimpered quietly but didn't complain. I was gonna get revenge when it was my turn to challenge him.

Annoyingly slowly, we reached the end of the line, an employee showing us where to stand. We were waiting in line for the last row but that didn't make any difference to me. It was all the same, wasn't it?

The wagon stopped in front of us abruptly, the occupants starting to laugh and chatter about the ride excitedly. There was the "tsshhhh" of the safety belts opening and people left through the exits, still talking agitatedly. Then, our doors opened.

I stumbled forward insecurely, Cas immediately following behind me and I sat down in my seat. An employee pressed down the lap bar and I winced at the sudden pressure on my ass. I wasn't gonna make this ride, I knew it already. But it was too late to leave now.

Something outside the wagon clicked -the sound of metal on metal- and we slowly began moving upwards. I kept my eyes closed from the second I was able to see the ground below us and silently prayed to whoever was listening.

Cas's hand took mine in a tight grip, trying to calm me down, and I listened to the wagon moving steadily, the rails clicking loudly underneath our feet. Suddenly, the clicking slowed down and I realized we must've reached the highest point.

The next thing I remember was racing down with breathtaking speed.

My eyes flew open widely and a scream escaped my mouth. The plug was forgotten momentarily and I threw my arms in the air excitedly, letting go off Cas's hand. It wasn't long though until I was painfully reminded of the toy inside of me.

The wagon raced back upwards, pressing me into my seat and simultaneously driving the plug right into my prostate and keeping it there. I let out a mix of a cry and a moan, my body going limb for a second and my vision going white. This was more intense than it had been the whole day! And I'd believed the car part to have been the worst.

The wagon sped along, up and down, taking turns and screws, all the while shifting and pushing the plug into me, making my dick throb painfully. I was dangerously close. If there was only one more thing as bad as that last fall, I was gonna come so hard I wasn't gonna remember my name.

And of course, because this day didn't give me a fucking break, I saw the last -and probably biggest- obstacle racing my way. I gulped and closed my eyes to prepare myself mentally but I couldn't have expected the improbable force of the looping.

I was being pressed into my seat, the world turning upside down and becoming blurry. I couldn't see a thing when the plug hit my prostate in the same spot it's been hitting the last five minutes and a loud groan left my mouth as I came as hard as I ever had. My body went numb, my eyes rolling inward involuntarily, and my head crashed against the seat painfully. I felt the warm liquid slowly running down my thigh but I didn't care about any of that. All I cared about was the complete and utter _bliss_ I was in because I finally, _finally_ came.

I felt the wagon come to an abrupt stop and I was pressed into my seat once again, whimpering from the overstimulation and struggling to recollect where I was.

"Dean," Cas said and nudged my shoulder. "You have to move or they'll ask you what's wrong!" he whispered at me frantically and I nodded in exhaustion. I didn't even want to know what I looked like in that very moment; unruly hair thanks to the wind, sweat shining on my forehead, tears streaking down my face, making my vision blurry, and a dumb grin mixed with the look of utter tiredness showing on my face.

Cas helped me get off the safety belt and dragged me out of the seat. I was thankful he was holding me up because I wouldn't have made it one single step without breaking down. The butt plug was still shifting ever so slightly with every move I made and it was simply too much.

"Are you okay, sir?" an employee asked when he saw me being held up by Cas's strong arms.

"He's alright, he's just feeling a little sick because of the ride," Cas lied. "Nothing to worry about, I'll get him to the restroom immediately!"

The employee frowned but nodded and Cas dragged me through the exit quickly.

"'M sorry, angel..." I muttered tiredly, thoughts still somewhat out of order, and Cas smiled at me sweetly.

"Nothing to be sorry about, big guy. You are one hell of a sight right now."

I couldn't help but snort and didn't say any more. I wouldn't have been able to say another sentence anyway.

We arrived at the bathroom soon after and I was dragged into one of the stalls immediately. Cas shut the door quickly and pressed me against the wall, his mouth breathing hot air into my ear, whispering, "You made some _very_ delicious sounds up there, Dean, did you know that? Almost made me come, too," he admitted and fixed me with a hungry stare. "But now is not the time," he decided and let go off me reluctantly. He pressed a gentle kiss against my lips and smiled.

"Now let's get this thing out of you before you hurt yourself. And we gotta get you cleaned up, too, your boxers won't keep your pants dry forever."

I nodded in relief and opened the buttons of my pants but that was about all I could do. I let Cas take care of the rest.

When I was eventually clean and had finally gotten over the unsatisfying feeling of emptiness, we left the bathroom stall together.

"Let's go home," Cas proposed and pressed a gentle kiss on my cheek. "You deserve it."

* * *

 "So, Cas, it's my turn, isn't it?" I whispered right into Cas's ear while letting my fingers trail over his naked body underneath me.

"Yes, Dean," Cas moaned and I pinched his nipples as a punishment. "Do not talk," I ordered. Cas only let out a stifled moan and I smirked to myself smugly.

"You were such a bad boy yesterday, Cas," I said and bit his earlobe lightly. "I have some special plans for you tonight..."


End file.
